Open AccessSynthesis of Fused and Linked Benzofurans from 2-Alkynylphenol Derivatives through Rhodium(I)-catalyzed Domino-type Addition Reactions
Author(s) -
Takanori Matsuda,
Shinya Abe,
Hirotaka Ito,
Tomoya Tsuboi,
Haruki Kirikae,
Masahiro Murakami
Publication year - 2018
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2018.888
Subject(s) - rhodium , benzofuran , indene , chemistry , domino , catalysis , indole test , cascade reaction , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry
A rhodium(I)-catalyzed domino-type sequential 5-endo/5-exo cyclization reaction of [(2-acylphenyl) ethynyl]phenols produces indene/benzofuran-fused alcohols. A moderate asymmetric induction is observed when chiral diphosphine ligands are used for rhodium. Indene/indole-fused compounds are synthesized by a similar reaction of [(2-acetylphenyl)ethynyl]anilines. The domino-type 5-endo/5-exo cyclization reaction is extended to substrates having two phenolic hydroxy groups. A linearly-fused array of five- and six-membered rings is constructed. Fused and linked benzofurans possessing 2-cyanoethyl side chains are also synthesized through sequential formation of C–O and C–C bonds.